Ted Wheeler: Understanding the Battle between Trump and the Mayor of Portland

At the center of it all is Ted Wheeler, the Democratic mayor of Portland. Lately, Wheeler has become President Donald Trump’s favorite punching bag, calling him “crazy” on Sunday. Wheeler retorted that Trump had “created hatred and division” in the country.

Our conversation, conducted via email and slightly edited for the feed, is below.

Cillizza: Let’s talk about Ted Wheeler * before * these protests started about 90 days ago in Portland. What was his general impression? Where did he come from?

Mapes: Wheeler, who comes from a wealthy Wood family and was once state treasurer with statewide ambitions, has had his struggles since being elected mayor in 2016. It’s part of it is because it’s one of the toughest jobs in Oregon politics. His last three predecessors resigned after a single term. (Portland has a very unusual form of local government.) OK, enough political science. Local politics took a decisive turn to the left during Wheeler’s stewardship and he struggled to respond to it. City council meetings have often turned into screaming matches, with protesters packing rooms to discuss police shootings, homeless policies and more. He is running for re-election this year and came very close in the May primaries to get the majority vote he needed to avoid a run-off. Her opponent is Sarah Iannarone, a local activist who runs to the left of Wheeler and has frequently participated in the protests. (Teressa Raiford, a black protest leader, is also leading a written campaign for the post).

Cillizza: Now, since the protests started: what has been the perception of how Wheeler conveyed all of this?

Mapes: Many activists laugh at him for failing to support larger cuts to the police budget – deferral of funding, if you will – and for allowing the Portland Police Office (which he directly oversees ) use tear gas regularly in the first weeks of protests. They called him “Tear Gas Teddy”.

At the same time, conservatives and many in the business world are complaining that he has not done enough to stop the non-peaceful side of the protests: vandalism, arson and violence against police (such as the launch projectiles and the radiation of laser lights into their eyes). Wheeler supported some cuts to the police budget and worked with Commissioner Jo Ann Hardesty, the only black member of the council and a longtime police spokesperson, to put a measure on the ballot by creating an independent police review system.

Cillizza: Before Trump arrived, was Wheeler taking the heat from other city poles or state poles? If so – who and why?

Mapes: He and Hardesty sometimes went to war with each other, and she repeatedly asked him to give her control of the police station.

Also, don’t forget that we are now in the second round of Wheeler’s cage match with Trump. The first took place in mid-July, when the administration moved police units from the Department of Homeland Security to Portland, apparently to protect the federal courthouse and other U.S. government facilities. This is when you started hearing reports of federal cops pulling protesters off the streets and pushing them into unmarked vans. The federal government has also stepped up gas attacks on protesters to a level never seen in an American city. Federal intervention – and Trump’s predictable inflammatory statements – have breathed new life into the protests and swelled crowds. Wheeler won national publicity when he showed up outside the Federal Courthouse one night to resist the gas attacks. He was derided by many protesters, but it’s fair to say that it has served him politically. And that seemed to affect him – he came back saying he realized how ineffective the ubiquitous tear gas attacks were in deterring protesters.In the end, it wasn’t Wheeler who found a way to get the federal forces out. the front line. It was Democratic housekeeper Kate Brown (who, ironically, won her post for the first time by replacing a resigning governor, ending Wheeler’s own hopes of running for the post). Brown brokered a deal to replace federal frontline forces with Oregon State Police soldiers, and that seemed to ease tensions for some time.

Cillizza: Trump attacking the mayor of Portland would, at first glance, appear to be good for Wheeler’s policy. True or false?

Mapes: A local pollster, John Horvick, who I spoke with joked that Trump’s attacks on Wheeler should be listed as an in-kind contribution to the mayoral re-election campaign. And at his press conference on Sunday, Wheeler was happy to repeatedly strike back at the president and urge him to drop his divisive rhetoric. But he was clear on what he was going to do in the future. And, again, Brown was the one with a concrete plan. She announced “a unified law enforcement plan to protect free speech and end violence and arson in Portland.” This includes strengthening the Portland Police Force with forces from other local police departments and the Oregon State Police, with additional assistance from the FBI and the United States Attorney’s Office.

Cillizza: Complete this sentence: “The Portland protests going national is a _________ thing for Ted Wheeler.” Now explain.

Mapes: I’m sorry, I left the business of political prediction after the 2016 election. As you might think, standing up to Trump is always good policy in Portland. But the loss of life (not just Saturday, but in the increasing number of shootings around the city recently) leaves the feeling of a city out of control. It’s not good for him. He’s probably still the front-runner for re-election, but voters in Portland are known to deliver election surprises. One thing seems pretty clear: he can forget about the state political office. Damn, I’m starting over, making predictions.

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